Catalytic, asymmetric α-chlorination of acid halides

被引：96

作者：

France, S ^{[1
]}

Wack, H ^{[1
]}

Taggi, AE ^{[1
]}

Hafez, AM ^{[1
]}

Wagerle, TR ^{[1
]}

Shah, MH ^{[1
]}

Dusich, CL ^{[1
]}

Lectka, T ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 13期

关键词：

D O I：

10.1021/ja039046t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present a full account of a tandem catalytic, asymmetric chlorination/esterification process that produces highly optically enriched (alpha-chloroesters from inexpensive, commercially available acid halides using cinchona alkaloid derivatives as catalysts and polychlorinated quinones as halogenating agents. We have performed kinetics and control experiments to investigate the reaction mechanism and establish conditions under which the reactions can be best performed. We have developed NaH and NaHCO3 shuttle base systems as the easiest and most cost-effective ways of conducting the reactions, rendering the methodology economically competitive with known chiral halogenation procedures. We have also demonstrated the utility of our reactions by converting the products to synthetically useful derivatives.

引用

页码：4245 / 4255

页数：11

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